BIOSYNTHETIC-STUDIES ON TAJIXANTHONE AND SHAMIXANTHONE, POLYKETIDE HEMITERPENOID METABOLITES OF ASPERGILLUS-VARIECOLOR

被引：36

作者：

AHMED, SA

BARDSHIRI, E

MCINTYRE, CR

SIMPSON, TJ

机构：

[1] UNIV BRISTOL,SCH MED,BRISTOL BS8 1TS,AVON,ENGLAND

[2] UNIV EDINBURGH,DEPT CHEM,EDINBURGH EH9 3JJ,MIDLOTHIAN,SCOTLAND

来源：

AUSTRALIAN JOURNAL OF CHEMISTRY | 1992年 / 45卷 / 01期

关键词：

D O I：

10.1071/CH9920249

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The biosynthesis of tajixanthone and related metabolites of Aspergillus variecolor has been studied by incorporation experiments with simple and advanced precursors labelled with the stable isotopes C-13, H-2 and O-18. Tajixanthone is shown to be derived through ring cleavage of an octaketide-derived anthraquinone with introduction of two dimethylallyl moieties. From the results of isotopic labelling experiments and chemical studies on model compounds, an overall biosynthetic pathway is proposed and information on the mechanisms of interconversion of proposed intermediates is obtained.

引用

页码：249 / 274

页数：26

共 48 条

[1] DICROTALINE - THE STRUCTURE AND SYNTHESIS OF DICROTALIC ACID
ADAMS, R
VANDUUREN, BL
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1953, 75 (10) : 2377 - 2379
[2] A CONVENIENT SYNTHESIS OF ISOTOPICALLY LABELED ANTHRAQUINONES, CHRYSOPHANOL, ISLANDICIN, AND EMODIN - INCORPORATION OF [METHYL-2H3]CHRYSOPHANOL INTO TAJIXANTHONE IN ASPERGILLUS-VARIECOLOR
AHMED, SA
BARDSHIRI, E
SIMPSON, TJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (12) : 883 - 884
[3] ANDERSON JJ, 1988, J AM CHEM SOC, V110, P5899
[4] BIOSYNTHESIS OF PHENOLS .21. MOLECULAR STRUCTURE OF ARUGOSIN, A METABOLITE OF A WILD-TYPE STRAIN OF ASPERGILLUS-RUGULOSUS
BALLANTINE, JA
FRANCIS, DJ
HASSALL, CH
WRIGHT, JLC
[J]. JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1970, (09): : 1175 - +
[5] BIOSYNTHESIS OF PHENOLS .24. ARUGOSIN-C, A METABOLITE OF A MUTANT STRAIN OF ASPERGILLUS-RUGULOSUS
BALLANTINE, JA
FERRITO, V
HASSALL, CH
JENKINS, ML
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1973, (17): : 1825 - 1836
[6] HYDROXYLATION OF ANTHRAQUINONES IN OLEUM AND IN SULFURIC-ACID
BANKS, HJ
CAMERON, DW
RAVERTY, WD
[J]. AUSTRALIAN JOURNAL OF CHEMISTRY, 1978, 31 (10) : 2271 - 2282
[7] STUDIES ON A SYNTHESIS OF (RS)-MEVALONIC ACID LACTONE
BARDSHIRI, E
SIMPSON, TJ
SCOTT, AI
SHISHIDO, K
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1984, (08): : 1765 - 1767
[8] BIOSYNTHESIS OF TAJIXANTHONE IN ASPERGILLUS-VARIECOLOR - INCORPORATION OF [H-2(3)]ACETATE AND [1,2-C-13(2)]ACETATE
BARDSHIRI, E
SIMPSON, TJ
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (04) : 195 - 196
[9] BIOSYNTHESIS OF TAJIXANTHONE AND SHAMIXANTHONE BY ASPERGILLUS VARIECOLOR - INCORPORATION OF O-18 GAS
BARDSHIRI, E
MCINTYRE, CR
SIMPSON, TJ
MOORE, RN
TRIMBLE, LA
VEDERAS, JC
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1984, (21) : 1404 - 1406
[10] BIOSYNTHESIS OF FUNGAL XANTHONE RAVENELIN
BIRCH, AJ
BALDAS, J
HLUBUCEK, JR
SIMPSON, TJ
WESTERMAN, PW
[J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1976, (08): : 898 - 904

← 1 2 3 4 5 →